Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand

Lang F.; Chen G.; Li L.; Xing J.; Han F.; Cun L.; Liao J.

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Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand

机译：铑通过叔丁烷亚磺酰基膦配体向2-硝基苯乙烯催化芳基硼酸的高对映选择性加成

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Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivities (up to 98%ee) by using tert-butanesulfinylphosphine as a ligand (see scheme). Based on this method, (R)-cherylline was synthesized in 70%overall yield.

机译：特别挑剔的配体！开发了在温和条件下向2-硝基苯乙烯中高效（S / C，底物/催化剂，最多500）Rh催化的芳基硼酸对映选择性加成的方法，收率优异（高达99％）和对映选择性（高达98％） ee）通过使用叔丁烷亚磺酰基膦作为配体（参见方案）。基于该方法，以70％的总收率合成了（R）-cherylline。

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《Chemistry: A European journal》 |2011年第19期|共4页
作者
Lang F.; Chen G.; Li L.; Xing J.; Han F.; Cun L.; Liao J.;
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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
asymmetric synthesis; cherylline; enantioselectivity; ligand effects; rhodium;

机译：不对称合成谢丽琳对映选择性配体效应铑;

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专利

1. Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand [J] . Lang F., Chen G., Li L., Chemistry: A European journal . 2011,第19期

机译：铑通过叔丁烷亚磺酰基膦配体向2-硝基苯乙烯催化芳基硼酸的高对映选择性加成
2. Deoxycholic Acid-Derived Biaryl Phosphites as Versatile and Enantioselective Ligands in the Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids to Nitroalkenes [J] . Varsha R. Jumde, Anna Iuliano Advanced synthesis & catalysis . 2013,第17期

机译：脱氧胆酸衍生的联芳基亚磷酸酯在铑催化的芳基硼酸与硝基烯烃的共轭加成反应中作为通用和对映选择性配体。
3. A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes [J] . Iain D. Roy, Alan R. Bums, Graham Pattison, Chemical Communications . 2014,第22期

机译：第二代配体，用于对映体铑催化的芳基硼酸加成至烯基氮杂芳烃
4. Preparation of Novel C_2-Symmetric Chiral Bicyclo2.2.2octadiene Ligands and Their Use for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids [C] . Yusuke Otomaru, Kazuhiro Okamoto, Kazuhito Ueyama, Symposium on Organometallic Chemistry . 2004

机译：新型C_2对称手性双环的制备2.2.2八二烯配体及其用于铑催化的不对称1,4-加入芳基硼酸的用途
5. Enantioselective Synthesis of Compounds Containing Bis-Benzylic Quaternary Stereocenters through Palladium-Catalyzed Conjugate Additions of Arylboronic Acids. [D] . Kadam, Abhishek Ashok. 2017

机译：通过钯催化芳基硼酸的共轭加成反应，对映选择性地合成含双苄基四元立体中心的化合物。
6. An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 14-Addition of Arylboronic Acids to αβ-Unsaturated Ketones [O] . Yasunori Yamamoto, Kazunori Kurihara, Yoshinori Takahashi, 2013

机译：N链双齿亚磷酰胺配体（N-Me-BIPAM）用于铑催化αβ-不饱和酮上芳基硼酸的不对称14-加成
7. Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to 2-Nitrostyrenes by tert-Butanesulfinylphosphine Ligand [O] . Lang Feng, Chen Guihua, Li Liangchun, 2011

机译：叔丁亚磺酰基膦配体对铑催化的芳基硼酸对2-硝基苯乙烯的高对映选择性加成。

Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand

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